MatchMaking
by Jck'sBrknHeart
Summary: John and Bobby believe their kids should get married, but Dean and Ashton have other things in mind.
1. Chicken Pox

**Disclaimer: **I do not own Supernatural or it's characters. Nor do I own the song 'This is My Idea' from Swan Princess - from which this story is based.

**Author's Note: **I know, I'm a bit cracked out sometimes. But if Bobby Singer had a daughter, I think this is a plausible scenario.

* * *

_The only point on which they didn't disagree  
Was that summertime was dreaded_

**I. If I Get Lucky I'll Get Chicken Pox.  
**

For as long as Dean Winchester could remember, he had spent parts of every summer at the Singer Salvage yard with his younger brother, Sammy. He was only six when his Dad started taking him there, and for as long as he could remember Bobby - owner of the Singer Salvage Yard - and John would tell him that one day he and Ashton Singer would wed. Quite honestly, Dean always thought they were both insane. Ashton wasn't exactly hunter material - she liked romantic, silly things like art and music. When Dean arrived at the Singer household Ashton was infallibly drawing something; though the particular something changed from year to year. She went through periods of morbidity, cartoons, and realistic portraits. Once she attempted to draw Dean himself, but found him too antsy to sit still long enough to capture the correct emotion. Yes, every summer Ashton would sit scribbling on Bobby's wooden floor with a piece of charcoal in hand - until one summer she wasn't.

For as long as Ashton Singer could remember, those damn Winchester boys would come to her home and invade her privacy. The little one, Sammy, wasn't so bad but the older one was far too cocky for her tastes. Even when he was young he boasted that he was the best shot in three states. Every summer he would come into her home, and stare at her as if she were an alien, then turn his attention to her father's piles of books of everything supernatural. Every summer John and Bobby would tell them how one day they would love each other. Every summer, Ashton despised the fact that she had to look at that goofy Dean Winchester from the moment she walked into the kitchen in the morning to the time she went to bed at night. She hated that he preferred shooting with her father to spending time with her. Ashton hated that Dean told her that she would never be a good shot because she was only a silly girl. Yes, every summer Dean would come to the Singer Salvage yard and work on the cars - until one summer he didn't.

And undeniably they both hated that they had to treat each other pleasantly until, at least, Bobby and John were out of the room plotting their to-be engagement. When they were twelve years old, Ashton 'accidently' broke three of Dean's fingers by shutting an old Plymouth's hood on it. That same summer Dean mysteriously broke his left leg in the Salvage Yard. John took Sammy and Dean from Bobby's early that summer. Still, no matter what abuse Dean was made to endure because Ashton was a girl (and John told him that it wasn't right to retaliate against a girl which only infuriated Ashton all the more), the patriarchs of the Winchester and Singer families insisted that one day they would think _very _differently about each other. Both Dean and Ashton rolled their eyes in scepticism while little Sammy smiled on - believing the elders fairy tales.

When Ashton was fifteen a peculiar thing happened - Bobby made her pack in a hurry and stuffed her into the old pick-up only to rush to Ohio in a hurry. The only thing he said was that they couldn't keep John and Dean waiting. She would have protested - told her father that she got car sick and didn't want to see the Winchesters, but with their particular line of work, Ashton sensed that something was very wrong. Just as every summer, Dean and Ashton were forced to be pleasant to each other.

"But Dad!" Dean protested, "There's a –"

John simply shook his head, "Properly greet Ashton and then we'll take care of it."

And after a very brief hug that was sufficiently awkward for both of them, Dean, Bobby and John all departed. Ashton never found out what it was that John and Dean needed help with and spent two days watching movies with Sam in John's hotel room. When they came back sufficiently bloodied and injured, Ashton knew that the job had been done. That was the only time Ashton saw the Winchesters that summer and had forgotten about them until the next summer.

When Dean arrived at the Singer Salvage Yard the summer of his seventeenth year, he suspected that the stay would be short-lived. He was basically an adult now, after all, and his father needed him more every day as much as he hated to admit it. He also suspected that she would be sitting on the couch, her glasses barely hanging on to her face as she perfected a portrait or added the finishing touches to a drawing. However, when he entered the room Ambre was no where to be seen. Bobby smiled at his friends and accepted them into his home alone.

"Where's she at?" Dean asked, curiously. He peeked around the corner into the turquoise colored room she called her own. It was empty and silent.

"Out back - she's almost always out back now." Bobby said.

Curious, Dean headed out back to the salvage yard. He was awe-struck when his eyes landed on the gorgeous woman bending over the engine of an American Muscle car that badly needed a paint job. A professional-looking camera sat on the roof of the car. She was wearing short, cut off denim shorts and an old flannel that had the sleeves rolled up to the elbows. Long black hair cascaded down the woman's back like a raven waterfall. Dean wondered who it could possibly be bending over the car and was almost dumbfounded when she straightened up. The woman turned out to be none-other than Bobby's only daughter. He was almost nauseous to think that he was getting turned on by Ashton Singer.

"Hey!" He called, "If you touch that car you'll break it!"

She looked up, her long hair swinging over her shoulder as she turned abruptly. It seemed as though she almost got whip-lash. She blinked a few times, "Dean?"

"No. The fuckin' candy man. Who else comes here every summer?"

Ashton sighed, "Some things never do change."

That summer Ashton tried and failed several times to get Dean to be a model for her. She claimed that it was a project for school but Dean never seemed to believe her. John and Bobby began to lose hope that they would ever have feelings for each other that weren't malicious or unpleasant. There was only one summer left until the metaphorical birds learned to fly on their own and if they couldn't learn to love each other in the eleven years they had known each other it was likely that they never would. The only one who never lost hope was Sam. It was late one night when thirteen year old Sammy stared at his brother from his spot on the floor.

"Why don't you go out with Ashton?" He asked.

Dean cocked a brow as he was staring back down at his younger sibling in disbelief, "She's not attractive that's why."

Sam could tell when his brother was lying and knew he was then, "I think she is."

"If you like her so much _you_ should ask her out." Dean snapped.

Sam smiled a bit to himself, "Aw, Come on Dean. I know you like her!"

"I'd like her better if she'd lose when we played poker," Dean murmured.

Sam smiled a bit to himself, "Maybe I will ask Ash out."

Dean mumbled something like 'the hell you will' and rolled over. The next day Sam sincerely planned on asking Ashton out, but both of the Winchester brothers were shocked to find out that she already had a date that Saturday night. Bobby was not particularly happy about it and when Ashton left with the tall, attractive eighteen year old, she was followed by Bobby and Dean in one of the more inconspicuous of Bobby's pick-ups. They picked up a few burgers and sodas for their stake-out. Bobby was more than amused that Dean was coming with him to stalk his daughter - he was ecstatic. After all, if Dean was jealous that meant he had feelings for her and Dean was _clearly_ jealous.

"Who is this guy anyway?" Dean asked after swallowing a bite of burger and washing it down with a sip of Coke.

Bobby swallowed a drink himself before replying, "Some hockey player that she met at school. Likes him a lot I reckon; she's been out with him a few times before this."

Dean nodded to himself as he watched Ashton with the guy. She hadn't even told Dean her boyfriend's name. The more he watched the more it pissed him off. There, in plain sight, another guy had an arm around her shoulders. He _constantly_ snuck in kisses while no one else was watching and Ashton only reciprocated.

Bobby watched Dean rather than his daughter - he trusted that she wouldn't get herself into _too_ much trouble - and found himself invariably amused by the young Winchester's facial expressions. There was little range; disgust to anger and back again.

"What do you think of him?"

Bobby shrugged, "Just as much of an idjit as the next eighteen year old male."

Dean looked over at his pseudo-uncle surprised. He didn't have more of an opinion of the boy his daughter was dating other than that he was a hormone-motivated teenager just like the rest of them. Wasn't he worried what would happen if Ashton told the boy what the family _really _did for "fun"? No, Ashton would never spill her secrets - she hadn't even told Sammy that she had a boyfriend and Dean knew that Sam called her when he had bad days.

It wasn't long before the date ended and Dean found that Bobby was speeding home so they wouldn't be caught. They were in luck, apparently, because they made it home only a few moments before her date's car pulled into Bobby's driveway. They were sitting nonchalantly on the couch talking about guns when she entered. She smiled brightly at them, "I know you followed me."

Bobby laughed, but Dean looked horrified. How had she known? It didn't matter, he decided as she sauntered into her bedroom, because she didn't seem to mind that she had been followed. She didn't seem to care in the slightest; in fact, Ashton seemed incandescently happy with herself. Dean got up and stood in her doorway, "What's his name, anyway?"

Ashton looked up, startled. She had been searching in her dresser for something when he came in. "His name is Evan," She replied, pushing her hair behind her ears and searching through the drawers once more. "Why are you asking, anyway? You've never been curious about my friends before, Dean."

He couldn't deny that this was true. Dean hadn't had the slightest interest in any of Ashton's affairs before this summer; he hadn't cared what kind of people she talked to or dated. But now he felt strangely jealous, "Just asking. What's he like?"

Ashton looked up skeptically from her search once more. Dean was sitting in her bed looking around her room now. There was a crucifix hanging above the head of her bed and a Kurt Cobain poster on the wall next to it. On the tall dresser against the wall was a huge Beauty and the Beast snow-globe that Bobby had gotten her one Christmas. Dean still found it odd that any offspring of Bobby's could be so - so feminine. There was a picture of her mother, a woman Ashton had never gotten the chance to know, next to the snow-globe. The older she got the more she started to look like the woman in the picture.

"He's ... not like you," She replied.

Dean rolled his eyes, "Of _course_ he's not like me. I'm–"

"He cares about me, more than I deserve him to," Ashton nodded sitting next to Dean and resting her head on his shoulder. It was hands-down the most affectionate she had ever been to him on her own accord. Dean realized then, that she wasn't just a pain in his ass that he had to deal with every summer for as long as he could remember. Ash was a human being just like he was - she had feelings, hopes, dreams.

"Why do you say that?"

Ashton shrugged as she grabbed a book from her night stand (The Stand by Stephen King) and opened the giant book to the middle where a bookmark saved her place. She began to read without really answering Dean at all. The next day John arrived to pick them up and, for once, Dean wasn't ecstatic to get away from Ashton - quite the opposite actually.

"She used to such an ... ugly duckling," He mumbled to himself as they drove away from the Singer Salvage Yard. John looked over at his son, one eyebrow raised in skepticism. Sammy was reading one of Ashton's Stephen King books in the backseat and ignoring the conversation.

Dean looked over at his father, "What?"

"You're mumbling to yourself about ducklings."

From the backseat Sam laughed.

"Ashton... she's –"

John smiled, knowingly, "Grown on you?"

Dean brooded in the passenger seat, "_No._ I'm just concerned that she's dating."

"_You_ date," John reminded.

"He doesn't date – " Sam began.

"Shut up Sam!"

The next winter and spring passed by more quickly that Dean had expected it to and, before he knew it, he was back at Bobby's house. When he walked in he wasn't surprised to find that Ashton wasn't drawing. Bobby told him she was in the backyard shooting. When Dean asked if that was with her camera or the shotgun, Bobby replied that he didn't know. A shot rang out signifying that it was the latter. Something must have been wrong.

Dean and Sam left the house and took an excessively long walk to get to where Ashton was. She was aiming the gun to shoot again when the Winchester boys approached. She seemed angrier than usual, but was just as attractive as the last time they had seen her.

"You alright?" Dean asked.

She turned around quickly and gave herself vertigo. Ashton leaned with her hands on her knees, to regain her balance. She shrugged, halfheartedly, "Not my best, I must admit."

"What's wrong?" Sam asked. He was only fourteen, barely pubescent, and still the only real gentlemen she had ever spoke to.

She smiled lightly at him, "Just one of those days. I didn't even know you two were on your way here."

"Bobby didn't tell you?" Dean asked, skeptically.

Ashton shrugged, "I'm sure he did. I probably wasn't paying attention."

A few weeks passed and seemingly Ashton had reverted back to her old self. She was spending her time drawing every second of every day and if she was not drawing she was taking photos. Sam was much more obliged to model for her than Dean had been in previous summers. It wasn't often that she would get film developed, but when she did Dean was always curious to see what she did. It surprised Ashton when, one day, she found Dean flipping through one of her various sketch-books in awe.

"What exactly are you doing Dean Winchester?" She asked, playfully.

"You're actually talented."

Ashton shrugged, "To your untrained eyes, maybe. What are you looking at?"

He held up the book; a portrait of himself was exposed to Ash. She felt nauseous and weak in the knees, but kept her composure. Truth was, she had dreams about Dean often. Corny, stupid, _romantic_ dreams about Dean Winchester. When she woke up, she often felt the unnerving, uncontrollable need to draw him - so she did.

"What did you do? Steal a picture from my dad?" Dean asked.

Ashton shook her head as she sat next to him, "Nope. I drew that from memory."

"From _memory?_"

"I've seen you every summer for twelve years and that surprises you? I practically draw Dad from memory unless he's researching and sitting for a long time."

"What about my Dad?" He asked, flipping through a few more pages.

"I had Dad take a picture last summer when John wasn't looking." She replied earnestly, "Why are you looking through this anyway?"

Dean shrugged and ignored the question before leaving the room to go work on one of Bobby's various junk-cars. Hardly a day had passed that Dean spent without thinking about Bobby Singer's daughter in a way that he really shouldn't have been. He could hardly describe her as sexy - at least not verbally, but when he felt like being truthful with himself he often thought she was very attractive indeed. Ashton, of course, had the same feelings for Dean - though she would not admit this to herself.

"So, I've got a question to ask you," Dean began a few days later as Ashton lay in her bed reading an issue of Rolling Stone that had the Foo Fighters on the cover.

She looked over at him, smiled slightly, and said, "So ask."

In all the years Dean had been asking girls out on dates, he had yet to be nervous about it. Well, that was until now. He felt nauseated as he stood there trying to keep his cool. "Do you want to go to get something to eat and maybe go to a movie on Friday?"

Ashton seemed to have stopped breathing and blinked once deliberately before speaking or even nodding. "Dean Winchester, are you asking me out on a _date_?"

Dean nodded unsmiling.

"Did John or Dad put you up to this?"

Dean shook his head.

"I suppose I _could_ go on a date with you," She replied nodding softly, "But you know they're going to follow us, don't you?"

He shrugged, "Maybe they will."

She smiled at him.


	2. All Their Pushing

**Disclaimer: **I do not own Supernatural or it's characters. Nor do I own the song 'This is My Idea' from Swan Princess - from which this story is based. A small part of this chapter is also inspired by the Bon Jovi song "I'll Be There For You."

**Author's Note: **I know, I'm a bit cracked out sometimes. But if Bobby Singer had a daughter, I think this is a plausible scenario.

* * *

**II. **

_Til now I never knew  
It was you I've been dreaming of. _

Ashton Singer examined her own face for the first time since she didn't know when. She sighed and wiped at a stray smudge of eyeliner. She was wearing a short blue and white striped dress with white flats. Yes, indeed, the reluctant daughter of Bobby Singer was dressed up for a date with Dean Winchester. The door was firmly locked in case she decided she didn't want to go through with it - but she found herself rising from the short stool in front of her vanity and opening the door. Bobby was waiting outside of her door and smiled. He was pleasantly surprised that she had put as much effort into getting ready for this date as she had for any of her prior dates.

She felt like she was going to prom as her father hugged her. Bobby and Ashton were not exactly known for being super affectionate as father and daughter, so Sam was compelled to watch in amazement as Bobby looked at his daughter in pride. He was busy reading another book of Ashton's - this time the Count of Monte Cristo - before she exited. Dean was outside, already in the car - too nervous to stay inside and wait for her to be ready.

She was carrying a small white purse as she forced herself out of the door way and looked into the car. Dean stared back as she shrugged. He couldn't help but laugh. She looked as nervous as he felt and when she got in the car beside him the anxiety at last eased. She was dressed up, and Dean thought that girls who didn't like their dates didn't bother with dressing up. Dean pulled the car into drive and left the Singer Salvage Yard cautiously.

Bobby and John, who had made it out to South Dakota for the occasion, were not far behind. The eldest of the Winchester and Singer clans made their way to the restaurant where their children were eating and were not surprised to see that they picked a window seat. Dean had an arm around Ashton who was chatting with kids from her graduating class. They were laughing and looked like they were just two normal teenagers on a date. John even saw Dean kiss Ashton's temple once - a gesture he had never before witnessed from his son. They stayed there until around 10, and got to the movie theater about ten minutes later.

"Our fathers are following us like creeps," Ashton noted, her arm wrapped comfortably around Dean's waist. Her head was resting right below his neck.

"You knew they would."

"But they're like, five feet behind us in sunglasses and reading newspapers," Ashton replied, "They're not even _trying_ to be inconspicuous!"

John chuckled from behind his newspaper.

Dean leaned in close, "I have an idea of how to ditch them." He whispered this so as to not alert their fathers of any mischief. When he glanced back at their fathers, neither seemed to be aware of what he had said.

"Really?" She smiled.

Dean nodded, "Just follow my lead."

Dean Winchester could certainly be sneaky when he wanted to be. First, he chose seats in the very back of the theater so that Bobby and John would have to turn around to watch them, lest they sit right next to their kids and end up screwing everything up. Second, Dean had chosen a horror picture to see. The dark scenes were perfect for a quick, conspicuous getaway. Indeed, within the first half hour of the film the two had fled the theater and escaped to the safety of Ashton's car. They took one look at each other after driving off and parking in a secluded area, and started making out.

When they got home, John and Bobby were sitting on the couch nonchalantly. John was describing to Bobby the last hunt he had been on (a shape-shifter, again). They both looked up at their children expectantly, and both children simply smiled back at them. "I'm going to bed," Ashton said and escaped into her room quickly before they could interrogate her.

The next morning she woke up to Sam's face staring at her. She blinked and pushed his head away as she rolled over. She tried to fall back asleep, but Sammy persisted in annoying her. "Please, **please** tell me that you didn't have sex with my brother." Her eyes popped open and she turned around so fast Sam was sure she had given herself a slight case of whiplash.

"Of course I didn't!" She screeched.

Sam smiled slightly, "Good."

It was another hour before she was out of the shower and ready for the day. To Sam, it was nice to see her in regular clothes again. Her dark hair was messy and curly. She smiled as she headed out back in a pair of black shorts and an old Bon Jovi t-shirt that Dean secretly wanted to steal from her. It wasn't exactly a mystery where she was going - Bobby had told both he and Dean that Ashton was still working on the Mustang. She was surprised, though, when she found Dean shirtless, sweaty, and covered in oil. He closed the hood as she approached and was wiping his hands on a dirty rag. He turned around and was sitting on the hood of the car when she approached.

"Does it run now?"

Dean jumped, slightly surprised by the added presence, but nodded none the less. She smiled, pleasantly surprised, and found herself running into Dean's arms. He hugged her tightly.

"Why did you fix it?" She questioned. Admittedly, Ash had been struggling to find out what was keeping it from running properly. She had too much pride to ask her father, Dean, or John for help - but was now visibly glad that Dean had helped her out.

He shrugged, "I knew you needed help."

Truth was, Dean had just wanted to impress her so that maybe he could try the dating thing again. After all, he had made an ass out of himself towards the end of the first date and could surely make up for it. He more than made it up on the second, third, and fourth dates. Sam started joking about the wedding date - he had never seen his older brother go on more than two or three dates with a girl unless she was having sex with her, and having sex Dean and Ashton weren't.

"Where are you two going now?" Bobby asked from the kitchen as he saw Dean pulling his daughter out of the house once more.

"He won't tell me!" She exclaimed and the screen door slammed behind them. Bobby looked over at Sam from his seat at the kitchen table and raised his brows.

Sam laughed as Bobby put a plate of food in front of him, "Dean's trying to be 'romantic'."

...

"Dean, where are you taking me, anyway?" Ash asked as they drove out to the middle of nowhere. She was surprised Dean could keep a secret from her for so long. It had been almost a week! It took at least forty-five minutes to get to where the oldest Winchester brother wanted to go. Ash was surprised; he hadn't taken her anywhere particular. It was literally the middle of nowhere. A dirt road led back to a tall oak tree surrounded by high, surprisingly green grass. He parked the Impala that his father had recently given to him, and looked over at her. There was a smirk on his handsome features.

Ash was no fool; she knew what exactly what he had wanted as soon as he parked the car in such a desolate locale. Whether he would get it or not was not was still a mystery to her. It all really depended on how he acted towards her. She was surprised how sweet Dean could be when he wanted something. Ashton had never seen Dean suck up to anyone to get what he wanted, but had often heard from Sam of his dating feats. She knew he was charismatic and charming, but she never knew that it would work on her.

Dean himself was surprised that he could charm his way into Ashton's pants. He thought she would refuse, but she didn't. It was, at that time, the best day of his life. It didn't last long, however, because Dean knew he was going to have to say goodbye one day. He wasn't nearly prepared for her reaction, nor was he really ready to leave her. And so, both of them would lose their happiness.

It was only a few days later, Dean couldn't remember how many, when he had to be the bad news bear. They were sitting on the hood of one of the many junked cars in Bobby's 'backyard' eating soft-serve Ice-Cream from the place up the street with the turtle-mascot. It was a perfect summer day. The sun was hot, the wind blowing gently. Ash was wearing an outfit that looked like it came from Daisy Duke's wardrobe on _Dukes of Hazzard_. Dean was surprised that Bobby let Ashton stroll out of the house in it. The shorts she were wearing, Denim cut-offs that were short enough to be considered hot-pants, fit her to a 'T.'

Dean found himself wanting her all over again. He glared momentarily at his younger brother who was also out in the sun enjoying an ice-cream cone. Sammy was cross-legged in the dirt, hardly paying attention to Dean or Ashton. The eldest of John Winchester's brothers inwardly groaned. Was this what it was like to break up with a girl you actually liked? Dean thought it was. It was going to be hard, maybe too hard, but John had told him that he couldn't do this for him. And Dean knew that, but he wished that John or Sam could all the same. Then, maybe Ash would hate them instead of him.

The ice-cream cones and Sammy gone from sight, Dean studied the young woman next to him. She'd come out of the other side of this okay; she was always stronger than Dean had thought. One day, she'd find someone that would be able to stay with her. Dean was convinced he wasn't that guy – even if John and Bobby had planned it that way. John had grown almost obsessed with killing the thing that killed their mother. He always insisted that they were getting close.

"Just a few more miles," John would tell his sons, "A few more months. You'll see."

The miles and the months passed all the same and they were no closer to whatever it was that killed Mary now than they were ten years ago. Dean wrapped an arm around Ashton, who in turn kissed his cheek, "What's wrong with you, Winchester?"

Dean looked up at her accusing green eyes. He couldn't lie to her, and he thought that maybe he loved her. He had known her for as long as he could remember. He didn't want to go. He wanted to stay here with her, but he knew he couldn't.

"Dean?" Her eyes were wide, and Dean wondered if she knew this was coming.

Dean nodded, more to himself than to her, "We're leaving soon."

"I expected you would be," She replied, coolly. It was around this time when they usually left Bobby's piece of South Dakota, yes. But she didn't quite understand.

He shook his head, "You don't understand, Ash."

"You always leave in mid-July. Why would this year be any different?"

Other than the fact that Ashton would probably be off at some Ivy League college or an art school while Dean would be hunting monsters that tried to eat people? Oh, nothing was different.

"We're _leaving_ Ash, as in, we're not coming back. Ever."

It took a minute for her to gather the information enough to comprehend. A look of pure confusion and anger distorted her usually gorgeous features, and when she was angry she sounded southern. Her accent would come to her and she would sound more like Bobby. Dean had expected all of these things, what he didn't expect was the slap in the face that came.

In their summers together he had suffered worse injuries: black eyes, broken bones, a bruised tail bone. But this was the one that felt worst. He knew he deserved it. Sammy and Dean left two days later. Ashton had not even come out of her room to say goodbye to Dean, and she would not allow him in either.

Later that afternoon, Ash left her bedroom and found her father reading lore about chupacabras. Her eyes were blood-shot, her hair stringy as if she not had a shower in a few days. Bobby set the book aside and motioned for his daughter to sit next to him. Instead, she sat on his lap and cried on his shoulder. (Literally on his shoulder, he felt the flannel dampening there.) The best way he knew to comfort his daughter was to rub her back and tell her it would be alright - but he couldn't do it this time.

"They'll be back," Bobby told her.

She shook her head, "It won't be the same. They'll stay for a day or two, then move on. We'll just be a free place to stay and eat. I don't want to see him again, Daddy."

It wasn't often that Ashton called her father "daddy," and she only played the innocent card when she needed to. He understood, and as much as he wanted to hate Dean for breaking his daughter's heart - he couldn't. He'd promised John he'd take care of those boys and he intended on following through with it. Besides that, he knew Dean didn't feel good about it and he understood why he had to do it. Bobby had seen the way John had been lately.

"He didn't want to leave," Bobby told his daughter softly, "Boy may be an idjit, but he wouldn't try to hurt you."

"Only because you or John would shoot him." She replied.

Bobby chuckled softly; he couldn't help it. Then he added, "Ashton, he had to. He didn't want to, but he had to. Do you understand?"

"Does it have to do with Mary?" She asked, quietly.

Bobby nodded.

"We don't go looking for the demon that killed Mom," Ash said, for the first time in her life sounding naive and unknowing.

The older, wiser Singer sighed, "That's because I didn't need to. There are some men like me, who can live their lives without vengeance or regret ever on their minds. It doesn't matter how precious something is if it is ripped away from them, they take it with a grain of salt and let the world go on as it would. Then there are men like John Winchester. He doesn't think Mary can rest as she ought to unless he finds and kills whatever it is that killed her. It's the only thing that's on his mind nowadays. It was easier when they were younger to flirt with the idea of them living a normal life again, and it seems impossible to John now - probably Dean too. You and Sammy, you've got a chance to get a different life. John, Dean, and myself don't have that chance."

She looked up at her father, wide-eyed and tired. Ash stole away to her bedroom once again in a few minutes and Bobby wondered if she would come out of the other side of this for the better.

"Huh," Sammy said to his older brother with a letter in his hands.

Dean looked over at Sam and raised a brow, "What is it?"

Sam shrugged, looking down at the letter once again. He continued reading. So far the letter told him to not expect to see Ashton when he got back into town. She would not be there. In fact, Ashton Elizabeth Singer wasn't even going to be in the same state anymore. This, of course, upset her father but he knew that this was for the best. Ash was going to an art institute in California. Bobby had to move her in next week. She didn't know to choose photography over drawing or vice versa.

"What're you reading now, geek boy?" Dean asked, ruffling his brother's hair as he feigned concentration on the highway in front of him. All he could read was "Sam." The handwriting was Bobby's - Dean could tell that without having to read it.

"A letter," Sam said, which really didn't answer his brother's question. He didn't plan on answering Dean's question, at all. When he asked "what're you reading" he meant, "why did bobby write to you." Sam could tell by the way that Dean was barely paying attention to the road.

"From?"

Sam looked up at his brother, but didn't say anything.


	3. A Romantic Notion

**Disclaimer:** As per usual, I do not own _Supernatural _**or any of the characters or related content. Nor do I own "This is my idea" the song from Swan Princess, which this story was inspired by.  
Author's Note: **Last Chapter of this story. Enjoy :) 

**

* * *

III.**

_What a good idea, such a powerful and magic potion, this is exactly my idea of love. _**  
**

Dean Winchester had never been one for huge romantic gestures. He had never had to be very romantic, nor had he ever had to make a huge gesture of affection for a woman before. Usually, he could handle a woman like a skilled painter could handle oils and a brush. He looked down into the show case skeptically. Silver, Gold, Topaz, Amethyst, Diamonds. A chupacabra was no match for Dean, but a fine jewelry store? The twenty-one year old Winchester sighed, and rested his head on his crossed arms. He should have just sent her a postcard and wished her luck with her new life, but no! He _needed_ to do this.

In the three years since the Winchesters had stopped coming to Bobby's house for an annual visit, Dean had changed quite a lot. And he couldn't stop thinking about Ashton, or the way she had looked that day when he told her he was leaving. She had moved out to California on a permanent basis, and had carried on with her studies. She split her time equally between realistic portraits and photography. The only reason Dean knew any of this was because he had drilled his little brother. As if that was pitiful enough, here he was at a jewelry boutique attempting to do something nice.

He had saved up money from hustling pool, playing poker, and credit card scams just to do this for her and, if he was rejected like he thought he would be, it would all be for nothing. Dean opened his eyes and stared down in to the case.

"Can I help you, uh, sir?" A soft, older woman's voice asked him.

Dean stood up and looked her over. Her hair was an auburn color, her cheeks pale; yup, she seemed to know her jewelry. "I'm looking to get a ring for my... friend."

"What does your, _friend_, like?"

The tall male shrugged, "I haven't seen her in a few years. It's sort of an 'I apologize for being a dick, will you marry me?' kind of thing."

"Oh, my. Well, what kind of hobbies does she have? What's her skin tone?" The woman questioned; she was smiling now, her thin skin pulled high over her cheeks. Apparently, this thing was right up her alley.

"She likes drawing, photography, art, and fast cars. Her skin is ... tannish?" Dean questioned. He didn't see what these questions had to do with anything.

The woman scurried off without saying much and when she returned, Dean had found what he had been looking for.

Ashton was lying on her stomach facing her boyfriend of four years and wondering how life had gotten so simple. Evan, the hockey player from her teens, had traversed across half the country to tell her that he loved her and wanted to be with her; they had been together ever since. Ash understood that her Dad didn't understand the life she was living, in the studio her and Evan shared in San Diego, and didn't expect he ever would. What she didn't understand was why Dean Winchester had not even tried to pick up a damn phone and call her. That's all it would have taken to win her back, and he couldn't pull it off. She sighed to herself and got out of bed.

After a long shower that did little to relax her, she went to the spare closet in the guest room. Pulling out a box of things left over from South Dakota, she sat down against the wall. She set the cardboard cover aside and dug through old photographs of John, Sammy, and her father. Slips of paper also resided in the box, each had a different hunter's number on it, just in case something came looking for her - though she never expected that to happen. Finally, she found what she was looking for. The small, navy colored velvet box felt unnaturally heavy in her hand. She snapped the lid open while holding her breath, and looked at the thing inside skeptically. There was a silver double-banded ring inside, and there was a small inscription on the inside of the band. It was nothing _too_ silly, but it embarrassed her nonetheless.

She could remember buying it two years before - the Winchesters had said they would drop by for Christmas - and remembered Bobby's peculiar look as he read the inscription. The small font read: 'Dum spiro, spero' Bobby was fluent in Latin and knew that it said, _'While I breathe, I hope_.' Bobby thought it meant that she hoped that one day he would be able to give up the life that John had set forth for him, and just be with her. Her father was not far off; in fact, he was spot on.

Ash realized she had been tearing up, and wiped a stray away from her face as she shoved the velvet box back into the shoe box. The door bell rang, and she got up from the floor, the box still on the floor, lying open. John's and Bobby's and Sammy's face stared up at the ceiling blankly.

He followed Bobby's directions back to Ashton's studio. Bobby had given Dean his blessing, but also warned him if he ever had to watch his daughter cry like a little girl again, that he would break all of his fingers and both of his legs. Dean had not taken this threat lightly. Pulling up to the apartment building, John Winchester's eldest son got out of his Impala and made haste inside. Her apartment was on the fifth floor and the elevator ride felt excruciatingly long. He buzzed her door, and in a few short moments, there she was.

But he had lost everything he ever had to say to her, and she found her way into his arms regardless. He kissed her longingly, and when they broke apart, he sighed. "Ash, I'm sorry. I didn't want to leave. I –"

"Dean, I know that. Why didn't you just say so sooner?" She asked.

Dean Winchester sighed, "I didn't... have the _courage_ to face you again, but now that I do." Dean pulled out the small turquoise colored box the woman at the jewelry shop had given him. He opened it, and Ashton stared down at it completely dumfounded. "Marry me."

The ring was beautiful, just like the man who had bought it, but the thought of a life like Dean's made her stomach churn. Evan was safe, reliable. He loved her, and he had not so much as looked at another woman while she was around. He supported her hobbies, hell he supported _her_. "Dean, I c-"

"Before you say that you can't. I'm not asking you to marry me today or tomorrow or even ten years from now. I'm just asking that you marry me one day; I can't leave here until you tell me that you can do that for me."

She was going to say something, but Dean cut her off again.

"I love you," He said simply, "And I know that you love me too. Dammit, we _belong_ together and–"

"Dean Winchester, shut up." She said calmly, "If you want me, you can have me whenever you're ready." It wasn't fair to Evan, she knew that, but Evan knew all about Dean. He had figured it out long ago, and had done little to change her mind. "Oh. Wait a minute!"

When she came back, she handed Dean the navy box.

"Men aren't supposed to get engagement rings." Dean said, raising a brow.  
She sighed and shook her head. Dean never failed to be a smartass, even now. "I got it for you for Christmas, two years ago. The year John said he'd show up, and left both my dad and I scratching our heads because he didn't. It's been rotting in my closet ever since."

Dean liked it, and liked it even more once he knew what the inscription meant. He felt the same way.

Evan looked down at the woman he had grown to love. One day, she was going to leave him for another man. Evan had known this since he met her as a teenager, but he just didn't know that he would ever meet that man. He briefly considered his odds if they got into a fight, and figured that he could win. He had two inches and thirty pounds on Dean Winchester, but he wouldn't even say a fighting word to him. Ashton loved him, and that mattered more to Evan than his own love for her.  
It was a waiting game now. How long would it take for Dean to sweep her away onto some imaginary white horse? Five years? Ten? Forty? If forty was the case, then maybe he would be dead and not have to deal with it at all. Evan thought that was unlikely. Dean would come back to get her much sooner than that.

And in the end, Evan was right. It took twenty years, a resurrection, and a friendship with one really hot angel, but he did come back. His white horse was a black 1967 Chevy Impala, and his shining armor was a plaid flannel button up, but he was just as beautiful and charming as any Prince she could remember in the Disney movies she had so loved as a child.

She had not been forced to leave Evan as she had once thought she would have been. He had said that he didn't want to be around when Dean came back. He had said it would break his heart, and that it would be easier for all of them this way. No body would have to feel guilty. No body would have to have a strained relationship. And by the time that Dean came back around, Ashton had been alone for five years. Of course, Bobby had objected to this, had begged Ashton to just come home, but she had refused.

In all the years she had lived alone, things had come after her. Things she had not expected: gods and angels and demons. They had all wanted to hurt Dean in the only way they knew how. To hit a vulnerable spot. But Ash had always come out on the other end alright. Sometimes out of her own resourcefulness, sometimes with Bobby's help, and other times – well, other times was just plain dumb luck.

And, as Dean Winchester enveloped Ashton Singer in his warm arms for the first time in twenty years, she finally felt like she was home.


End file.
